The present invention relates to novel personal product or detergent compositions comprising glycosylamides as well as to novel processes for their preparation.
Carbohydrate based surfactants are potentially of great value because they represent a naturally-occurring source of renewable raw materials that are synthetically versatile, inexpensive, optically pure and environmentally friendly.
The glycosylamide compounds used in the novel detergent and personal wash compositions of the invention are themselves not novel. For example, U.S. Pat. No. 4,574,122 to Kruger et al. (assigned to Bayer), teaches substituted O-acyl glycosylamides for use in pharmaceutical compositions to stimulate the immune system's response and antibody production. Related U.S. Pat. No. 4,683,222 to Stadler et al. (assigned to Bayer) teaches N-glycosylated carbonamide derivatives which can be used for increasing immune system antibodies.
U.S. Pat. No. 4,680,287 to Lockhoff et al. (assigned to Bayer) also teaches these compounds, in this case used as growth promoters in live-stock feeding.
In U.S. Pat. No. 4,710,491, Lockhoff et al. (assigned to Bayer) teaches a method of combatting rheumatic diseases which comprises administering to a patient afflicted therewith with an amount of these compounds effective to combat the disease.
U.S. Pat. No. 4,891,425 to Lockhoff et al. (assigned to Bayer) teaches the use of these compounds as medicaments.
U.S. Pat. No. 4,923,980 to Blomberg teaches a process for the manufacture of a gel product, wherein a reducing sugar is covalently coupled to a matrix of a gel product. The matrix provides amino groups which can react with a reducing sugar to form a glycosylamine that is stabilized by acylation to form the corresponding glycosylamide. The invention has utility in affinity chromatography wherein the glycosylamide is coupled onto a solid carrier or matrix such as a gel.
J. Carbohydrate Chemistry 8 (4), 597-611, 1989 to Kallin et al. teaches the copolymerization of N-acryloylglycosylamines with acrylamide which are useful as antigens in immunoassays.
Methods in Enzymology 167, 272 (1988) to Bendall et al. teaches the use of N-methyl-N-decanoyl maltosylamine as a surfactant for photosystem II. While recognizing this compound to be surface-active, there is no teaching or suggestion that the compounds are used in detergent and/or personal product compositions.
J. Org. Chem. 25, 1322, (1960) to Onodera et al. teaches a method of acylating unsubstituted glycosylamines by reacting anhydrides with glycosylamines in methanol at 50.degree. C.
French Patent No. 2,657,611 and Tetrahedron Letters 32 (12), 1557 (1991) to Ecole Superieure de Chimie de Rennes describes a process for preparing glycosylamides without prior protection of hydroxyl groups by using reagents (2-acylthio-5-methyl-1,3,4-thiadiazoles or 3-acyl-5-methyl-1,3,4-thiadiazole-2-(3H)-thiones) more selective than acyl chlorides. While recognizing these compounds are nonionic surface active agents, there is absolutely no teaching or suggestion that the compounds be used in detergent and/or personal product compositions.
French Patent No. 2,695,127 to Eridania Beghin-Say teaches a process for making glycosylamines in a diluted solvent and for preparing glycosylamides from glycosylamines and activated alkanoic acids. Again, there is absolutely no teaching or suggestion of using the glycosylamides as surfactants in detergent and/or personal product compositions.
French Patent No. 2,661,413 to Stepan teaches N-alkyl lactylamines and methods for preparing. Example 7 at pages 9-10 is an N-acetyl nonyl lactosylamine wherein the R' group is COCH.sub.3 and therefore could be defined as an amide. There is no teaching or suggestion that such as amide could be used in detergent and personal product compositions. Indeed, in none of the examples which discuss surfactancy properties (i.e., surface active properties of Examples 1-5 and 8 of French Patent No. 2,661,413) is the amide exemplified in a detergent and/or personal product composition. Moreover, a general description of surface active properties (for the amines not the glycosylamides) is not a teaching or suggestion to use the compounds of the invention in detergent and/or personal product compositions in any event. Similarly, data about protein solubilization (Example 9) is neither a teaching or suggestion to use such compounds, particularly the glycosylamides of the invention, in detergent or personal product compositions.
Langmuir 11, 3644 (1995) to Costes et al. teach the preparation of N-acetyl-N-alkyl lactosylamines as surfactants for the extraction of proteins in pharmacological applications. Again, there is no teaching or suggestion to use glycosylamides in detergent and/or personal product compositions.
EP Application No. 0,515,283 (1992) to El Ghoul et al. (assigned to Stephan) teaches acetylated glycosylamides useful as solubilizing agents in the isolation of membranous proteins. Again, there is no teaching or suggestion to use glycosylamides in detergent and/or personal product compositions.
EP Application No. 0,550,099 (1993) to Au et al. (assigned to Unilever PLC) teaches the use of glycosylamides as antimicrobial agents (anti-plaque) in oral hygiene compositions. Again, there is no teaching or suggestion to use glycosylamides in detergent and/or personal product compositions.
Finally, in an article in Carbohydrate Research, 266, pp 211-218 (1995), Lubineau et al. teach preparation of N-acylglycosylamines as carbohydrate-based detergents. Some of the compounds made are set forth at top of page 214.
The compounds taught in this reference, (1) always have a hydrogen atom attached to the nitrogen (R.sub.2 group) and (2) always have an R.sub.1 group which is saturated and is not interrupted by a heteroatom (e.g., oxygen, sulfur or nitrogen).
Applicants have found that such compounds in which there is an attached hydrogen group at R.sub.2, have much higher Krafft points, are far less soluble and consequently cannot be effectively formulated in detergent and personal product formulations.
By contrast, if the R.sub.2 group is substituted with C.sub.1 to C.sub.30 alkyl group, preferably a C.sub.1 to C8 alkyl group rather than hydrogen; or if the R.sub.1 group contains a heteroatom such as O, S or N; or both; solubility is enhanced (lower Krafft point), such that the glycosamide compounds of the invention become more water soluble and can be readily and effectively formulated in detergent and personal product compositions.
Further, the fact that there is a hydrogen on the amide functional group and no heteroatom on the R.sub.1 group (resulting in lower solubility) itself demonstrates that the compounds of Carbohydrate Research 266, pp 211-218 (1995), were not contemplated for use in detergent or personal product compositions. Also, novel methods of manufacture of glycosylamides have not been disclosed in the art.
In short, the use of the glycosylamide compounds of the subject invention in various detergent and personal product composition is simply unknown. The general surfactancy of the certain glycosylamide compounds are known, but this does not teach or suggest the use of the glycosylamide compounds of the invention in specific detergent and/or personal product compositions and, if anything, the use of such compounds in purely pharmaceutical applications actually teaches away from their use in the applications of the invention.
Thus, the ability to find a naturally derived, environmentally friendly, readily biodegradable, solid sugar based nonionic surfactant and a viable, cost-effective, commercially feasible method for their manufacture is a significant achievement.
Accordingly, it is an object of the present invention to provide new and improved detergent and personal product compositions that have excellent cleansing properties.
It is another object of the present invention to provide detergent and personal product compositions that have enhanced copious persistent foam.
It is another object of the invention to provide liquid detergent and personal product compositions that have enhanced thick viscosity which allows effective bottle packaging.
It is another object of the present invention to provide stable clear liquid detergent and personal product compositions which do not become turbid on produce sedimentation upon standing.
It is another object of the present invention to provide nonionic sugar based surfactants that dissolve readily and foam well in water.
It is still another object of the present invention to provide a viable, commercially feasible process for the manufacture of nonionic sugar based surfactants.
It is still another object of the present invention to provide an improved process for the manufacture of alkyl glycosylamides.
It is yet another object of the present invention to prepare alkyl glycosylamides in good yield, high purity and desirable color without hydroxyl group protection, oligomerization or polymerization.
These and other objects will become readily apparent from the detailed description that follows.